The Third Story with Leo Sidran

Ben Wikler has spent his career moving between comedy and politics, communication and organizing. Growing up in Madison, Wisconsin, a city shaped by civic engagement, academic inquiry, and the satirical spirit that gave rise to The Onion, he developed a worldview in which humor isn't a distraction from democracy, but one of the ways people learn to trust one another enough to participate in it.
Wikler has become one of the country's most closely watched political organizers. He was the chair of the Democratic Party of Wisconsin from 2019-2025, and is the author of This Is the Plan: How to End America's Meltdown and Save Democracy.
But this conversation isn't about campaign tactics or election cycles. Instead, it's about the values and experiences that shaped him: the Wisconsin Idea, the role of humor in public life, the changing media landscape, and why curiosity, optimism, and solidarity remain essential ingredients of democratic life. Recorded at the Madison home where Ben grew up, and where he and his wife are now raising their own family, this is a conversation about place, purpose, and what it takes to keep believing in the promise of democracy.
www.third-story.com
www.leosidran.substack.com
www.wbgo.org/podcast/the-third-story

A conversation with Ben Sidran, from Greece on America's 250th birthday, about jazz, democracy, identity, and what remains when the scaffolding begins to shake.

Before The Irish Goodbye became one of the most acclaimed debut novels of 2025, Heather Aimee O'Neill spent years quietly writing it while building a career helping other writers tell their stories.
Here, she discusses the vulnerability of ambition, the challenge of living an authentic life, and the strange transition from observer to protagonist when a lifelong dream finally comes true.
www.third-story.com
www.leosidran.substack.com
www.wbgo.org/podcast/the-third-story

Saxophonist and bandleader Lakecia Benjamin has become one of the most dynamic voices in jazz today. Here she talks about hanging up on Clark Terry, finding her way from Washington Heights to the international stage, and how the mentors, heroes, setbacks and aspirations that shaped her journey continue to inform her new album, We Dream.
www.third-story.com
www.wbgo.org/podcast/the-third-story

Miles Davis spent his life searching. He changed the sound of jazz repeatedly, assembling generations of musicians around him and pushing constantly toward something new. Few artists loom so large over the history of the music.
To mark what would have been his 100th birthday today, I'm revisiting a rare 1986 conversation between Miles and my dad, Ben Sidran, recorded on the terrace of Miles' Malibu home. 
At a time when Miles was reticent about revisiting his past, in this interview he reflected on Kind of Blue, his early musical development and influences, as well as his ideas about creativity, individuality and what it means to make a meaningful artistic contribution.
To start the episode, Ben and I had our own conversation about the Miles interview, his memory of doing it, how it resonated at the time and how it resonates today. In the 40 years since it was recorded, the interview has become one of the definitive documents of Miles' thinking during that period.
Ben's original interview with Miles Davis was originally made for his NPR program Sidran on Record, and is now part of his Talking Jazz project. The full archive is available at https://talkingjazz.bandcamp.com/album/talking-jazz
Today's episode image is borrowed from "Notes from the Ertegun Jazz Hall of Fame" produced by Quoted Studios and Jazz at Lincoln Center.